1,4-bis(6-phenylfulven-6-yl)benzene | 138062-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis(6-phenylfulven-6-yl)benzene
• 英文别名: 1,4-Bis[cyclopenta-2,4-dien-1-ylidene(phenyl)methyl]benzene
• CAS: 138062-34-7
• 化学式: C₃₀H₂₂
• 分子量: 382.505
• InChiKey: JQQLFXDSOHWDIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-bis(6-phenylfulven-6-yl)benzene 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 122.0h， 生成 1,4-bis<7-(phenylmethylidene)-2,3-diazabicyclo<2.2.1>hept-2-en-7-yl>benzene
  参考文献：
  名称：

  Trapping of cyclopentanediyl and trimethylenemethane triplet diradicals with the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl

  摘要：

  Nitroxide trapping constitutes a convenient and effective alternative to dioxygen for the detection of triplet diradical intermediates. Thus, photolysis of the azoalkanes 1a-c in the presence of the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl produced the bisalkoxyamines 3a-c by trapping of the transient triplet diradicals 5a-c. The resulting bis-adducts 3a-c were fully characterized, and their regio- and stereochemistry were established on the basis of spectral and X-ray data for trans-3a and trans-3b. The novel bis-azoalkane 1d was prepared and its photochemical loss of nitrogen studied in the presence of the above nitroxide or dioxygen as scavengers. In the case of the nitroxide, the tetrakis-adduct 3d was obtained, tentatively assigned in view of its thermal instability, while with dioxygen the stable bis-peroxide 4d was isolated and rigorously characterized. Instead of concurrent double denitrogenation to afford the high-spin non-Kekule species 5d or its low-spin quinoid diradical 5d', stepwise loss of dinitrogen and trapping is proposed to be the pathway to these products.

  DOI：

  10.1021/jo00029a036
• 作为产物：
  描述：

  1,4-联苯酰基苯 、 环戊二烯 在 sodium 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以56%的产率得到1,4-bis(6-phenylfulven-6-yl)benzene
  参考文献：
  名称：

  Trapping of cyclopentanediyl and trimethylenemethane triplet diradicals with the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl

  摘要：

  Nitroxide trapping constitutes a convenient and effective alternative to dioxygen for the detection of triplet diradical intermediates. Thus, photolysis of the azoalkanes 1a-c in the presence of the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl produced the bisalkoxyamines 3a-c by trapping of the transient triplet diradicals 5a-c. The resulting bis-adducts 3a-c were fully characterized, and their regio- and stereochemistry were established on the basis of spectral and X-ray data for trans-3a and trans-3b. The novel bis-azoalkane 1d was prepared and its photochemical loss of nitrogen studied in the presence of the above nitroxide or dioxygen as scavengers. In the case of the nitroxide, the tetrakis-adduct 3d was obtained, tentatively assigned in view of its thermal instability, while with dioxygen the stable bis-peroxide 4d was isolated and rigorously characterized. Instead of concurrent double denitrogenation to afford the high-spin non-Kekule species 5d or its low-spin quinoid diradical 5d', stepwise loss of dinitrogen and trapping is proposed to be the pathway to these products.

  DOI：

  10.1021/jo00029a036

文献信息

• Trapping of cyclopentanediyl and trimethylenemethane triplet diradicals with the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl
  作者：Waldemar Adam、Steven E. Bottle、Ralf Finzel、Thomas Kammel、Eva Maria Peters、Karl Peters、Hans Georg Von Schnering、Leonhard Walz

  DOI：10.1021/jo00029a036

  日期：1992.1

  Nitroxide trapping constitutes a convenient and effective alternative to dioxygen for the detection of triplet diradical intermediates. Thus, photolysis of the azoalkanes 1a-c in the presence of the nitroxide 1,1,3,3-tetramethyl-1,3-dihydroisoindolin-2-yloxyl produced the bisalkoxyamines 3a-c by trapping of the transient triplet diradicals 5a-c. The resulting bis-adducts 3a-c were fully characterized, and their regio- and stereochemistry were established on the basis of spectral and X-ray data for trans-3a and trans-3b. The novel bis-azoalkane 1d was prepared and its photochemical loss of nitrogen studied in the presence of the above nitroxide or dioxygen as scavengers. In the case of the nitroxide, the tetrakis-adduct 3d was obtained, tentatively assigned in view of its thermal instability, while with dioxygen the stable bis-peroxide 4d was isolated and rigorously characterized. Instead of concurrent double denitrogenation to afford the high-spin non-Kekule species 5d or its low-spin quinoid diradical 5d', stepwise loss of dinitrogen and trapping is proposed to be the pathway to these products.